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Although the exact mechanism of the Pd-catalyzed hydrostannation is still unknown, it is generally believed that it proceeds via an initial hydropalladation rather than a palladastannation step (see ref 10). We propose that, in this case, nonconcerted migratory insertion results in hydride approaching and adding to a triple bond faster than palladium. Consequently, palladium adds last and to a more hindered site, overall affording α-stannylated stilbenes. For a similar steric effect governing regiochemistry of carbopalladation in the Heck reaction, see: Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
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